Phenyltrimethylammonium Salts as Methylation Reagents in the Nickel-Catalyzed Methylation of C−H Bonds

Methylation of C(sp2)−H bonds was achieved through the NiII‐catalyzed reaction of benzamides with phenyltrimethylammonium bromide or iodide as the source of the methyl group. The reaction has a broad scope and shows high functional‐group compatibility. The reaction is also applicable to the methylat...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-02, Vol.55 (9), p.3162-3165
Main Authors: Uemura, Takeshi, Yamaguchi, Mao, Chatani, Naoto
Format: Article
Language:English
Subjects:
Aliphatic compounds
Amides
Bonding
chelation assistance
C−H activation
Iodides
Methylation
Nickel
phenyltrimethylammonium iodide
Reagents
Salts
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Summary:Methylation of C(sp2)−H bonds was achieved through the NiII‐catalyzed reaction of benzamides with phenyltrimethylammonium bromide or iodide as the source of the methyl group. The reaction has a broad scope and shows high functional‐group compatibility. The reaction is also applicable to the methylation of C(sp3)−H bonds in aliphatic amides. Its all about Me! The methylation of C(sp2)−H bonds was achieved through the NiII‐catalyzed reaction of benzamides with phenyltrimethylammonium bromide or iodide as the source of the methyl group. The reaction has a broad scope and shows high functional‐group compatibility. The reaction is also applicable to the methylation of C(sp3)−H bonds in aliphatic amides.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201511197